Aminoalkylsilicon compounds and process for producing same



Un sd S ate Pa AMINOALKYLSILICON COMPOUNDS AND PROCESS FOR PRODUCING SAME Victor B. Jex, Kenmore, and Donald L. Bailey, Snyder,

N.Y., assignors to Union Carbide Corporation, a corporation of New York 1 No Drawing. ApplicationOctober 12,1956 Serial No. 615,466

Claims. (Cl. 260-448.8)

This: invention relatesin general to the synthesis of organosilicon compounds. More particularly, the invention is concerned with the production of organosilicon compounds containing, among other possible functional groups, an amino functional group linked to the silicon atom or atoms thereof through an aliphatic hydrocarbon J. l nkage in a position removed from the silicon nucleus y at least three carbon atoms and to organosilicon conipounds containing an aminobutylsilyl grouping as new compositions of matter. The invention is further concerned with a process for producing compounds of the general class described. 7 v The present invention is based, in. part, upon our discovery that organosilicon compounds containing an amino group attached to the silicon atom thereof through a polymethylene linkage can be produced by the hydrogenation of cyanoalkyl silicon compounds. The overall reaction can be graphically represented by the following equation:

NC CH SlE +H H NCHz (CH ,siE I wherein (a) can be any number having a value greater than one.

According to our studies, the basic reaction as illustrated above is equally applicable to the cyanoalkylalkoxysilanes and the cyanoalkylpolysiloxanes. Typical of the syanoalkylalkoxysilanes suitable for use as our organoe silicon starting materials arethose compounds represented by the structural formula:

. R NC(CHz),,S i(0R)s-, I wherein R represents either an alkyl group or an aryl group, R represents an alkyl group, y is a number having a value of from 0 to 2 and (a) is a number having a value. greater than one. Illustrative of the alkyl groups which R and R can represent include methyl, ethyl, propyl, butyl and the like, while illustrative of the aryl groups which R can represent are phenyl, naphthyl, tolyl and the like. Such cyanoalkylal-koxysilanes include betacyanoethyltriethoxysilane, beta-cyanoethyltripropoxysilane, beta-cyanoethylmethyldiethoxysilane, betacyanoethylphenyldiethoxysilane, beta cyanoethyldimethylethoxysilane, beta cyanopropyltriethoxysilane, gammacyanopropyltriethoxysilane, gamma cyanopropylmethyldiethoxysilane, gamma cyanopropylphenyldiethoxysilane, delta-cyanobutyltriethoxysilane, delta-cyanobutylmethylcliethoxysilane, delta cyanobutylphenyldiethoxysilane and the. like. u

Cyanoalkylpolysiloxanes suitable for use as our starting materials, are those polysiloxanes which" contain the structural unit: A,

1; [NC(OH2)'1SiO :q]

wherein R and y have the values defined above. Such V be employed, however, no commensurate ically .equivalent amounts; however we prefer to employ polysiloxanes include: the trifunctional cyanoalkylpoly- 'siloxanes (i.e. where y'=0) such as betal-cyanoethylpolysiloxane, gamma-cyanopropylpolysiloxane,' the, di- 5 of a cyanoalkyl silicon compound, hydrogen and a suitable catalyst and heating the mixture to a temperaturev sufiiciently elevated to cause the starting materials to react. There results or is produced by the addition of hydrogento-the cyano group and by subsequent reactions, a. mixture of the mono-, bisand tris-aminoalkyl silicon compounds, e

In carrying out our process, the hydrogenation of cyanoalkyl silicon compounds is best conducted in a closed system, as for example in a pressure vessel, or' in apparatus designed for flowing reactants which permit the maintenance of a closed system at pressures aboveatmospheric' pressure. To provide for the carrying out of the reaction at. a desirable'rate we-prefer to charge the system, within which. the reaction is conducted, to a considerable pressure with the hydrogen reactant. In general we have found it convenient. to conduct the reaction under a pressure of atleast 500 pounds per square inch.

The temperatures at which hydrogen and a cyanoalkyl silicon compound react to form an aminoalkyl silicon compound are not narrowlycritioal and can vary'over a wide range. We have conducted the reaction at temperatures as low as C. and at temperatures as high as C. with good results. Temperatures below 80 C. as for example about 50, C. and above 140 C. can' advantage is obtained thereby.

Therelative amounts of hydrogen and the cyanoalkyl silicon compound employed in our process are not' narr-owly critical. The compounds can be employed in chem hydrogen in an amount above that required to completely reduce the cyanogroup of the cyanoalkyl silicon reactant. An excess of hydrogen is also, as hereinabove disclosed, desired to provide suflicient pressure for the reaction to proceed at a desirable rate. We have found it convenient to employ the hydrogen reactant in an amount ,of from about 2 to about 20 chemical equivalents perch e'mical equivalent of the cyanoalkyl silicon reactant.

As hereinabove described the hydrogenation of cyanoalkyl silicon compounds produces a mixture of the mono, bisand tris-substituted amines. The overall reaction can be graphically represented by the following equation which depicts, for the purpose of illustration, the reaction of hydrogen with beta-cyanopropyltriethoxysilane:

We have found that the relative proportion of the mono-,'

bis-and tris-substi-tuted amine products of our process can be controlled by conducting the reaction in the pres- Patented. Mar. 29, 19.6.0.

mono-substituted amine compounds. tration, when gamma-cyanopropyltriethoxysilane is hydrogenated in the absence of ammonia a yield of less than 25 mole percent of ,delta-aminobutyltriethoxysilane is obtained. On the other hand, when the same reaction is conducted in the presence of ammonia in an amount of about 20 moles of ammonia per mole of gamma-cyanopropyltriethoxysilane employed, the yield of delta-aminobutyltriethoxysilane is increased to about 80 mole percent. The amount of ammonia which can be employed in our process to increase the yield of the mono-substituted amine reaction products can vary over a wide range. We can employ the ammonia in an amount of from about 1 toabout 50 moles and higher per mole of the cyanoalkyl silicon compound present in the reaction mixture. Amounts of ammonia in greater mole ratios than those suggested above can also be employed. However, no material advantage is obtained thereby. We 'can employ as catalysts for the reaction between hydrogen and the cyanoalkyl silicon compounds, any of those metals or compounds known to be effective in promoting hydrogenation reactions. The platinum metals such as platinum and palladium can be employed alone or in combination with a suitable inert support, or in combination with gamma-alumina. We can also employ nickel as well as Raney nickel and Raney cobalt and certain cyclopentadiene metals such as bis(cyclopentadienyl)nickel. The reaction between hydrogen and the cyanoalkyl silicon compounds can be carried out within a suitable liquid organic compound in which our starting materials are soluble and with which they are non-reactive. Suitable for use in our process are: the alkanols as for example ethanol, propanol and the like, the aromatic hydrocarbons as for example benzene, toluene and the like. The amount of the liquid organic compound which can be employed as a solvent for the reaction is not narrowly critical and can vary over a wide range. We can employ such compounds in an amount of from about 50 to about 500 parts per 100 parts of the cyanoalkyl reactant.

Our process makes possible the production of alkoxysilylbutylamines, which as far as is known have not been heretofore prepared. Such compounds are characterized by properties not found or even suggestive of their lower homologues as for example, the alkoxysilylpropylamines which are disclosed and claimed in our copending U.S. application Serial No. 483,421, filed January 21, 1955, now U.S. Patent No. 2,832,754, granted April 29, 1958, or the alkoxysilylmethylamines of the art which are known to be unstable.

The alkoxysilylbutylamines of our invention can be graphically represented by the formula:

wherein R' represents an alkyl group such as methyl, ethyl, propyl, butyl and the like, R represents a hydrocarbon group including an alkyl group such as methyl, ethyl, propyl, butyl and the like, or an aryl group such as phenyl, t-olyl, naphthyl and the like, and (x) and (y) are integers having values of from to 2. Illustrative of the alkoxysilylbutylamines of the invention are triethoxysilylbutylamine, tripropoxysilylbutylamine, diethoxymethylsilylbutylamine, diethoxyethylsilylbutylamine, diethoxyphenylsilylbutylamine, ethoxydimethylsilylbutylamine, bis(triethoxysilylbutyl)amine, tris(triethoxysilylbutyl)amine, bis(diethoxymethylsilylbutyl)amine, tris(diethoxyphenylsilylbutyl) amine and the like.

The compounds of our invention, particularly the dialkoxymethylsilylbutylamines, unlike their homologues, referred to above, are extremely poisonous and find wide utility in the preparation of pesticides, fungicides, insecticides and herbicides as is hereinafter set forth. Such compounds have also been employed as sizes for fibrous glass materials as is disclosed and claimed in copending By way of illus- U.S. application Serial No. 615,482 filed concurrently herewith. It has also been found that our compounds by virtue of their amino group are useful in the synthesis of monomeric and polymeric organosilicon compounds. Our process is broadly applicable to the production of aminoalkyl silicon compounds including monomers which can be represented by the formula:

wherein R, R, (x) and (y) have the values previously described, (b) has a value of at least 3 and polymers 7 which can be represented by the unit:

' hydrogenation of cyanomethylalkoxysilanes results in a reaction which does not produce the expected aminoethylalkoxysilanes. In alike manner, the reaction disclosed and claimed in our above-identified copending application for the production of aminopropylalkoxysilanes, namely the reaction of ammonia with a gamma-chloropropylalkoxysilane, is not applicable to the production of beta-aminoethylalkoxysilanes by the reaction of ammonia with betachloroethylalkoxysilanes. As the compounds are apparently not stable, they cannot be recovered.

,The following examples are illustrative of the invention:

EXAMPLE 1 Preparation of triethoxysilylbutylamine To a 300 cc. pressure vessel were charged 0.21 mole (49-grams) of gamma-cyanopropyltriethoxysilane and 3 grams of Raney nickel. The vessel was then cooled in Dry Ice to a temperature of about 7 8 C. and 4 moles (68 grams) of liquid ammonia added thereto. The vesselwas closed and hydrogen gas charged thereto until the.pressure therein reached 2000 pounds per square inch. It was calculated that about 0.5 mole of hydrogen gas was added to the vessel. The vessel was then placed in a rocking autoclave and heated to a. temperature of 100 C. for a period of 21 hours. After heating, the 'vesselwas cooled to room temperature and the liquid product filtered and transferred to a 100 ml. distilling flask and fractionally distilled under reduced pressure through a 50 cm. Vigreaux column. Triethoxysilylbutylamine distilled at 123124 C. under a reduced pressure of 15 mm. Hg. The compound has a density at 25 C. of 0.934 gram per cc. and a refractive index at 25 C. N of 1.4222. Analyses for the element content, neutralization equivalent and molarrefraction of the product were conducted and the results obtained compared with the calculated values for triethoxysilylbutylamine. The obtainedandcalculated data appear below.

Calculated Observed Molar Refraction 63. 7 64.1 Neutralization Equivalent 235. 4 238. 5 Percent OEt 57. 4 55.1 Percent 0..-. 51. 0 47. 9 Percent 10.7 10.4 Percent Si. 11. 9 12. 2 Percent N- 5. 9 5. 7

A yield" of about 85 mole percent was obtained. The same reaction conducted in the absence of ammonia resultcd in a yield of about 20 mole percent.

EXAMPLE 2 Preparation of mono-, bisand Iris(triethoxysilylbutyl)amine To a 3 liter pressure vessel were charged 0.73 mole (168.4) grams) of gamma-cyanopropyltriethoxysilane, 217.4 grams of ethanol and 2 grams of Raney nickel. The vessel was sealed, evacuated, filled with anhydrous ammonia until the pressure in the vessel reached about 130 p.s.i. gauge. Hydrogen was then charged to the vessel until the pressure therein reached 1500 p.s.i. The vessel was placed in a rocking autoclave and heated to a temperature of 120 C. for a period of.26 hours. After heating the vessel was allowed to cool to room temperature and the liquid product filtered to remove the catalyst and solids therein. The filtrate and washings were charged to a Vigreaux column, together with the filtrates and washings obtained from several additional reactions conducted in the manner set forth above, and fractionated. Triethoxysilylbutylamine distilled at a temperature of 67' to 74 C. under a reduced pressure of 0.65-0.75 mm. Hg and bis(triethoxysilylbutyl)amine distilled at a temperature of 144 to 160 C. under a reduced pressure of 0.55 mm. Hg (refractive index at 25 C. 1.43l4l.4369) while tris(triethoxysilylbutyl)- amine distilled at a temperature of 222 to 230 C. under a reduced pressure of 0.45 mm. Hg (refractive index at 25. C. 1.4444).

EXAMPLE 3 Preparation of diethoxymethylsilylbutylamine To a 300 ml. stainless steel pressure vessel were charged 0.36 mole (72.5 grams) of gamma-cyanopropylmethyldiethoxysilane, 80 ml. absolute ethanol and 3.6 grams of Raney nickel. The vessel was cooled in Dry Ice to a temperature of about -78 C. and 0.4 mole (8 m1.) of liquid ammonia added thereto. The vessel wassealed and hydrogen charged thereto until the pressure therein reached approximately 1100 p.s.i. gauge. The vessel was then placed in a rocking autoclave and heated to a temperature of 80 C. After heatingvfor a period of one hour the pressure in the vessel dropped to about .100 p.s.i.g. and hydrogen again charged thereto until the pressure therein reached 1100 p.s.i. gauge. The vessel was heated for an additional five hours at a temperature of 80 Cfafter which time it was allowed to cool to room temperature. The liquid product was filtered and the filtrate added to a distilling flask and fractionated under a reduced pressure. There was obtained 66.85 grams of diethoxymethyl silylbutylamine (a water white liquid) distilling at a temperature of 70 to 75 C. under a reduced pressure of 2.2 to 2.5 mm. Hg. Titration of the product by the standard HOl method indicated that the amino content of the compound was 7.9 percent and :the neutralization equivalent was 205.3 (theoretical amino content for diethoxyrnethylsilylpropylamine7.8 percent and theoretical nuetralization equivalent-205.3).

Delta-aminobutylmethyldiethoxysilane has a boiling point of 93 to 96 C. under a reduced pressure of 9 mm;

Hg and a boiling point of 217 C. at atmospheric pressure. The compound has a refractive index (N 1.4293, a viscosity at 25 C. of 2.0 cs.) a flash point of 200 F.

and is completely miscible with acetone, benzene, di-

methyl Cellosolve, chloroform, dioxane, ethanol, ethyl acetate, heptane and toluene.

.rnoIe (50 grams) of gamma-cyanopropyldimethylethoxysilane, Raney nickel and 6 moles (100 cc.) of liquid 6 ammonia. The vessel was sealed 'and'hydro'gen charged thereto until the pressure therein'reached 1950 p.s.i.'gauge. The vessel was then placed in a rocking autoclave'and heated to a temperature of 115 C. for a period of 3 days. After heating the vessel was cooled to room temperature, the product removed therefrom and filtered. Distillation of the filtrate gave 25.0 grams of dimethylethoxysilylbutylamine boiling at a temperature of 80 to 82 C. under a reduced pressure of 10 mm. Hg. The compound was identified by infra-red. analysis and by neutralization equivalent (theory 175, found 176). 1

' EXAMPLE 5 Preparation of triethoxysz'lylpentylamine anhydrous ethanol and 2 grams of Raney nickel. The

vessel was closed, chilled with Dry Ice and anhydrous am= monia charged thereto until the pressure therein reached 125 p.s.i. gauge. Hydrogen was then charged to the vessel until pressure therein reached approximately 1500 p.s.i. gauge. The vessel was then placed in a rocking auto:- clave and heated at a temperature of 130 C. for a period of 12 hours. On cooling the vessel a pressure drop of 800 p.s.i. gauge was observed and hydrogen was again charged thereto until the pressure therein reached 1500 p.s.i. gauge. The vesel was reheated at a temperature of 130 C. for another 12 hour period. After cool ing the vessel to room temperature, the contents thereof Calculated Observed Molar Refraction 68. 3 68. 7 Neutralization Equivalent. 247. 4 245 Percent O 53. 4 52.9 Percent H 11.0 10.8 Percent Si 11.8 11.3 Percent N 5. 7 5. 7

EXAMPLE 6 1 Preparation of triethoxysilylpropylamine To a 300cc. stainless steel pressure vessel were charged ..0.22 mole (48.5 grams) of beta-cyanoethyltriethoxysilane and 3 grams of Raney nickel. The vessel was then cooled in Dry Ice to a temperature of approximately 78 C. and 7.4 moles ml.) of liquid ammonia added. The vessel was then closed and hydrogen gas charged thereto until the pressure therein reached 1900 pounds per square inch. The vessel was then placed in a rocking autoclave and heated for 16 hours at a temperature of 100 C. After heating, the vessel was cooled to room temperature and it was noted that the residual pressuretherein was 1150 pounds per square inch. The products were filtered under argon through Magnesol (a commercial filter aid) to remove thenickel catalyst and the solids obtained were washed with anhydrous ether. The filtrate and wash ings were distilled in a 50 cm. Vigreaux column under reduced pressure. Triethoxysilylpropylamine distilled at 221 C. (741 mm. Hg) has a density of 0.937 gram per cc. at 25 C. and a refractive index, N of 1.4198. Further analyses of the product for element content ncu- I 'tralization equivalentand molar refraction were. con-' i ducted and the data obtained compared with those cal- 7 culated values forltriethoxysilylpropylamiue.' The obtained and calculated data appears below.

The compound was also identified by infra-red analyses.

- EXAMPLE 7 mn0-, his and tris(triethoxysilyl-beta- Preparation of methyl-propyl) amines To a 300cc. pressure vessel were charged 72 grams of betacyanopropyltriethoxysilane, 29 grams anhydrous ethanol and-2 grams of bis(cyclopentadienyl)nickel. The vessel was sealed and anhydrous ammonia charged thereto until the pressure in the vessel reached 125 p.s.i. gauge. Hydrogen was then charged to the vessel until the pressure therein reached 1600 p.s.i. gauge. The vessel was then placed in a rocking autoclave and heated to a temperature of 130 C. for a period of 12.5 hours. After heating the vessel was cooled to room temperature and the product (a liquid) filtered to remove the catalyst and solids therein which were subsequently washed with anhydrous isopropyl ether. The filtrate and washings were combined and distilled under reduced pressure to obtain the mono-, bisand tris(triethoxysilyl-beta-methylpropyl) amines. The boiling points and the neutralization equivalent for each of the amines appear in the table below.

EXAMPLE 8 Preparation of diethoxymethylsily lpropyltzmine To a 3 liter steel pressure vessel were charged 0.5 mole (91 grams) of beta-cyanoethylmethyldiethoxysilane, 200 ml. of methanol and 2 grams of Raney nickel. The vessel was then cooled in Dry Ice to a temperature of about 78 C. and 10 moles (200 ml.) of ammonia added thereto. The vessel was sealed and hydrogen charged thereto until the pressure within the vessel reached 1400 p.s.i.g. The vessel was then heated at a temperature of 110 C. for a period of 24 hours. After heating, the vessel was cooled to room temperature and the liquid product ,was placed in a distilling flask and fractionated. There was distilled 23.9 grams of diethoxymethylsilylpropylamine at a temperature of 58 to 60 C. under a reduced pressure of 2.2 mm. Hg. Identification of the compound was also established by elemental analysis for nitrogen. The compound has a refractive index at 25 C. N3 of 1.4270.

' EXAMPLE 9 :Attempted preparation of triethoxysilylethylamine by the reaction of hydrogen with cyanomethyltriethoxysilane 'ammonia charged thereto until the pressure therein compound wherein reached p.s.i.g. Hydrogen was then charged to the vessel until the pressure therein reached 1200 p.s.i.g. The vessel was placed in a rocking autoclave and heated to a temperature of C. for a period of 12 hours. The vessel was then cooled and the product therein comprised for the most part a non-distillable residue which indicated that decomposition of the starting cyauo compound had occurred. The product did not contain aminoethyltriethoxysilane.

EXAMPLE 10 Based on quantitative data, delta-aminobutylonethyldiethoxysilane is poisonous to animals such as rabbits and the like by means of skin absorption. However, the compound is not poisonous to such animals when they are subjected to the compound by swallowing or inhalation.

What is claimed is:

'- 1. An alkoxysilylbutylamine having the structural formula:

wherein R is taken from the group consisting of alkyl and aryl groups, R represents an alkyl group, and (x) and (y) are numbers having a value of from 0 to 2.

2. A trialkoxysilylbutylamine. Triethoxysilylbutylamine. A dialkoxyalkylsilylbutylamine. Diethoxymethylsilylbutylaminc. An alkoxydialkylsilylbutylarnine. A process for preparing an aminoalkylsilicon compound, wherein the amino group is removed by at least three carbon atoms from silicon, which comprises forming amixture of (a) hydrogen, (b) a cyanoalkylsilicon the cyano group is removed by at least two carbon atoms from silicon and wherein said silicon is connected to at least one member from the class consisting of alkoxy and silicon through silicon to oxygen to silicon linkage, the remaining unfilled valences of said silicon being satisfied by a member from the class consistiug of alkyl, aryl, alkoxy and silicon through silicon to oxygen to silicon linkage, and (c) a hydrogenation catalyst, and heating the mixture to a temperature sufiiciently elevated to cause said hydrogen and cyanoalkylsilicon compound to react to produce said aminoalkyl silicon compound.

8. A process for preparing aminoalkylsilicon compound, wherein the amino group is removed by at least three carbon atoms from silicon, which comprises forming a mixture of (a) hydrogen, (b) a cyanoalkylsilicon compound wherein the cyauo group is removed by at least two carbon atoms from silicon and wherein said silicon is connected to at least one member from the class consisting of alkoxy and silicon through silicon to oxygen to silicon linkage, the remaining unfilled valences of said silicon being satisfied by a member from the class consisting of alkyl, aryl, alkoxy and silicon through silicon to oxygen to silicon linkage, (c) a hydrogenation catalyst, and (d) ammonia, and heating the mixture to a temperature sufficiently elevated to cause said hydrogen and cyanoalkylsilicon compound to react to produce said aminoalkyl silicon compound.

9. A process for preparing an aminoalkylsilicon compound, wherein the arnino group is removed by at least three carbon atoms from silicon, which comprises forming a mixture of (a) hydrogen, (b) a cyanoalkylsilicon compound wherein the cyauo group is removed by at least two carbon atoms from silicon and wherein said silicon is connected to at least one member from the class consistiug of alkoxy and silicon through silicon to oxygen to silicon linkage, the remaining unfilled valences of said silicon being satisfied by a member from the class consisting of alkyl, aryl, alkoxy and silicon through silicon to oxygen to silicon linkage, (c) a hydrogenation cat- Jalyst, (d) ammonia, and (e) a liquidorganio compound own-nor with which said hydrogen and cyanoalkylsilicon compound are non-reactive and in which said hydrogen, cyanoalkylsilicon compound and aminoalkylsilicon compound are soluble, and heating the mixture to a temperature sufiiciently elevated to cause said hydrogen and cyanoalkylsilicon compound to react to produce said aminoalkyl silicon compound.

10. A process for preparing an aminoalkylalkoxysilane wherein the amino group is removed by at least three carbon atoms from the silicon atom thereof which comprises forming a mixture comprising (a) hydrogen, (b) a cyanoalkylalkoxysilane wherein said cyano group is removed by at least two carbon atoms from the silicon atom thereof and wherein the remaining valences of said silicon atom are connected to from one to three alkoxy groups and from to 2 hydrocarbon groups selected from the class consisting of alkyl and aryl, the sum of said alkoxy groups and hydrocarbon groups connected to silicon being equal to 3, and (c) a hydrogenation catalyst, and heating the mixture to a temperature sufficiently elevated to cause said hydrogen and cyanoalkylalkoxysilane to react to produce said aminoalkylalkoxysilane.

11. A process for preparing an aminoalkylalkoxysilane wherein the amino group is removed by at least three,

carbon atoms from the silicon atom thereof which comprises forming a mixture comprising (a) hydrogen, (b) a cyanoalkylalkoxysilane,wherein said cyano groupis removed by at least two carbon atoms from the silicon atoms thereof and wherein the remaining valences of said silicon atom are connected to from one to three alkoxy groups and from 0 to 1 hydrocarbon groups selected from the class consisting of alkyl and aryl, the sum of said alkoxy groups and hydrocarbon groups connected to silicon being equal to 3, (c) a hydrogenation catalyst, and (d) ammonia, and heating the mixture to a temperature sufiiciently elevated to cause said hydrogen and cyanoalkylalkoxysilane to react to produce said aminoalkylalkoxysilane.

12. A process for preparing aminoalkylalkoxysilanes which comprises forming a mixture of hydrogen, a cyanoalkylalkoxysilane, having the structural formula:

wherein R is taken from the group consisting of alkyl and aryl groups, R' represents an alkyl group, (a) is a number having a value of greater than one and (b) is a number having a value of from 0 to 2, ethanol, ammonia, and Raney nickel and heating the mixture to a temperature of from about 80 to 140 C. to cause said hydrogen and cyanoalkylalkoxysilane to react to alkylalkoxysilanes.

13. A process for preparing aminoalkylpolysiloxanes which comprises forming a mixture of hydrogen, a cyanoalkylpolysiloxane having the structural formula:

If: [NO (CH2) .Sio

produce amino to cause said hydrogen and cyanoalkylpolysiloxane to react to produce an aminoalkylpolysiloxane.

14. A process for producing diethoxymethylsilylbutylamine which comprises forming a mixture of hydrogen,

7 gamma-cyanopropylmethyldiethoxysilane, Raney nickel and ammonia and heating the mixture to a temperature of from about C. to about 140 C. to cause said hydrogen and gamma-cyanopropylmethyldiethoxysilane to react to produce diethoxymethylsilylbutylamine.

15. A process for producing triethoxysilylpropylamine which comprises forming a mixture of hydrogen, betacyanoethyltriethoxysilane, Raney nickel and ammonia and heating the mixture to a temperature of fromabout 80 C. to-about 140 C. to cause said hydrogen and beta-cyanoethyltriethoxysilane to react to produce triethoxysilylpropylamine.

References Cited in the file of this patent UNITED STATES PATENTS 2,557,802 Sommer June 19, 1951 2,715,133 Speier Aug. 9, 1955 2,754,284 Speck July 10, 1956 2,754,311 Elliott July 10, 1956 2,762,823 Speier Sept. 11, 1956 2,832,754 Jex et a1. Apr. 29, 1958 FOREIGN PATENTS 1,065,545 France Jan. 13, 1954 1,116,726 France Feb. 6, 1956 OTHER REFERENCES Petrov et al.: Doklady Akad. Nauk, USSR, vol. (February 1955), pp. 71114. 

1. AN ALKOXYSILYLBUTYLAMINE HAVING THE STRUCTURAL FOR MULA?
 7. A PROCESS FOR PREPARING AN AMINOALKYLSILICON COM POUND, WHEREIN THE AMINO GROUP IS REMOVED BY AT LEAST THREE CARBON ATOMS FROM SILICON, WHICH COMPRISES FORMING A MIXTURE OF (A) HYDROGEN, (B) A CYANOALKYLSILICON COMPOUND WHEREIN THE CYANO GROUP IS REMOVED BY AT LEAST TWO CARBON ATOMS FROM SILICON AND WHEREIN SAID SILICON IS CONNECTED TO AT LEAST ONE MEMBER FROM THE CLASS CONSISTING OF ALKOXY AND SILICON THROUGH SILICON TO OXYGEN TO SILICON LINKAGE, THE REMAINING UNFILLED VALENCES OF SAID SILICON BEING SATISFIED BY A MEMBER FROM THE CLASS CONSISTING OF ALKYL, ARYL, ALKOXY AND SILICON THROUGH SILICON TO OXYGEN TO SILICON LINKAGE, AND (C) A HYDROGENATION CATALYST, AND HEATING THE MIXTURE TO A TEMPERATURE SUFFICIENTLY ELEVATED TO CAUSE SAID HYDROGEN AND CYANOALKYLSILICON COMPOUND TO REACT TO PRODUCE SAID AMINAOALKYL SILICON COMPOUND. 